Process for the production of antiseptically-acting bodies.



s'rns rro.

REINHOLD FREIHERR VON WALTHER, 0F DRESDIEN, GERMANY, ASSIGNOR T0 '1. I.BIEDEL ACTIENGESELLSGI-IAFT, 0F BERLIN, GERMANY.

PROCESS FOR THE PRODUCTION OF ANTISEPTICALLY-ACTING BODIES.

Be it known that I, REINHOLD FREIHERR VON WALTHER, professor, a subjectof the Emperor of Germany, and residing at 15 Muenchenerstrasse,Dresden, Saxony, Germany, have invented certain new and usefulImprovements in Processes for the Production of Antiseptically-ActingBodies, of which the following is a specification.

The 6 halogen 1 methyl-3-oxybenzol-4- carboxylic-acids have. hithertobeen produced only according to a single exceedingly complicated andtechnically impracticable process (compare Berliner Berichte 26, (1893)page 1851). The products themselves have remained entirely unnoticed.

I have now made the surprising discovery that the mono-halogensubstitution products of the metacresotinic acid possess strongantiseptic properties which is the more surprising as these propertiesare not possessed by the meta-cresotinic acid which up to now has notbeen used therapeutically. A further advantage of the mono-halogenproducts consists in the very slight degree in which they are poisonous.It has been found for example by comparative experiments that the 6chloro 1 methyl-3-oxybenzol- L carboxylic-acid is twice to four timesless poisonous than salicylic acid. This again was not before seenbecause of the cresotinic acids according to Frankel(Arzneimz'ttelsynthese, 1919., page 229) are more poison ous thansalicylic acid. By the process here inafter described I have beenenabled to produce this valuable disinfectant without difficulty.

By using the Kolbe-Schmidt process, the p-chloro-m-cresol (OH: CH(31:3:1: 6) is extremely readily converted into the 6chloro-1-methyl-3-oxybenzol-lrcarboxylicacid. Whereas theoretically theformation of 2 isomeric mono-carboxylic acids from p-chloro-m-cresol wasto be expected, it is surprising that only a single uniform acid wasobtained in an almost quantitative yield.

G'opies of this patent may he obtained for five cents each, byaddressing the Specification of Letters Patent.

Patented June 22, 1915.

Application filed March 16, 1914. Serial No. 825,187.

Example: Dry p-chloro-m-sodium-cresolate is heated in autoclaves at apressure of about five atmospheres for six hours in an atmosphere ofcarbon di-oXid to about 160 C. When heated over 180 C. the mass ischarred. The product obtained is dissolved in boiling water and filteredand this 6 chloro-l-methyl-3-oxybenzol- 1-carboxylicacid is precipitatedby means of diluted hydro-chloric acid in the form of a lightcrystalline powder. For a further purification the acid may bere-crystallized from aqueous alcohol. From water it is crystallized inmicroscopical needle-shaped bodies and from alcohol in flat prismaticcrystals. Its melting point is at 205 C.

I claim:-

1. The process of producing antiseptic 6-halogen-1-methyl-3-oxybenzol--carboxylic acid which comprises heating 6-halogen-3- sodium-cresolatewith carbon dioxid under pressure to relatively high temperatures.

2. The process of producing antiseptic 6-chloro-3-oxybenzol4-carboxylicacid which comprises heating 6-chloro-3-sodium cresolate with carbondioxid under pressure to relatively high temperatures.

3. The process of producing antiseptic 6-chloro-3-oxybenzol-4-carboxylicacid which comprises heating 6-chloro-3-sodium cresolate with carbondioxid under pressure to a temperature of about 160 C.

4:. The process of producing antiseptic 6 chloro1-methyl-3-oxybenzol-4-carboxylic acid which comprises heating dryparachloro-metasodiumcresolate at a pressure of about five atmospheresin an atmosphere of carbon dioxid to a temperature of about 160 C.

In testimony whereof I have signed my name to this specification in thepresence of two subscribing witnesses.

REINHOLD FREIHERR VON WAL'IHER.

Witnesses:

Lno A. BERGHOLZ, PAUL ARRAS.

commissioner of Patents,

Washington, D. O.

It is hereby certified that the name of the assignee in Letters PatentNo.

1,144,270, granted June 22, 1915, upon the application of ReinholdFreiherr von Walther, of Dresden, Germany, for an improvement inProcesses for the Production of Antiseptically-Acting Bodies, waserroneously Written and printed as T. D. Biedel Actiengesellschaft,Whereas said name should have been Written and printed I. D. RiedelActiengesellschaft; and that the said Letters Patent should be read withthis correction therein that the same may conform to the record of thecase in the Patent Office.

Signed and sealed this 2nd day of November, A. D., 1915.

' [SEAL] R. F. WHITEHEAD,

Acting Commissioner of Patents.

